N-Boc-反式-4-羟基-L-脯氨酸甲酯合成路线 （共 102 条）
反应条件
in N,N,N',N',N'',N''-hexamethylphosphoric triamide
1.) 23 h, room temp., 2.) 2 h, 50 - 60 degC;
参考文献
Dormoy, J.-R.
Synthesis, 1982 , # 9 p. 753 - 756
参考文献
Klein, Scott I.; Dener, Jeffrey M.; Molino, Bruce F.; Gardner, Charles J.; D'Alisa, Rose; Dunwiddie, Christopher T.; Kasiewski, Charles; Leadley, Robert J.
Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 18 p. 2225 - 2230
反应条件
1: 89 percent / NaH / dimethylformamide / 3 h / 20 °C
2: 100 percent / aq. NaOH / tetrahydrofuran / 3 h / Heating
View Scheme
参考文献
Chiba, Jun; Takayama, Gensuke; Takashi, Tohru; Yokoyama, Mika; Nakayama, Atsushi; Baldwin, John J.; McDonald, Edward; Moriarty, Kevin J.; Sarko, Christopher R.; Saionz, Kurt W.; Swanson, Robert; Hussain, Zahid; Wong, Angela; MacHinaga, Nobuo
Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 8 p. 2725 - 2746
反应条件
1: sodium periodate; ruthenium trichloride
View Scheme
参考文献
Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V.
Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849
反应条件
1: 98 percent / pyridine / 0 - 25 °C
2: 6.74 g / NaN3 / dimethylformamide / 60 °C
3: 2N NaOH / dioxane / 1 h / 25 °C
4: conc. HCl / dioxane / 2 h / 50 °C / pH 2
View Scheme
参考文献
Le Quement, Sebastian T.; Ishoey, Mette; Petersen, Mette T.; Simonsen, Pernille M.; Holck, Nanna S.; Nielsen, Thomas E.
Tetrahedron Letters, 2011 , vol. 52, # 52 p. 7049 - 7053
反应条件
1.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C
2.1: diethylamino-sulfur trifluoride; ethanol / dichloromethane / 18 h / 20 °C / |Inert atmosphere
3.1: potassium hydroxide
4.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / dichloromethane / 15 - 20 °C
4.2: 0.33 h / 20 °C
View Scheme
参考文献
Jansen, Koen; Heirbaut, Leen; Verkerk, Robert; Cheng, Jonathan D.; Joossens, Jurgen; Cos, Paul; Maes, Louis; Lambeir, Anne-Marie; De Meester, Ingrid; Augustyns, Koen; Van Der Veken, Pieter
Journal of Medicinal Chemistry, 2014 , vol. 57, # 7 p. 3053 - 3074
反应条件
1: 91 percent / (COCl)2; Et3N; DMSO / CH2Cl2 / -40 - 20 °C
2: 89 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C
View Scheme
参考文献
SPINIFEX PHARMACEUTICALS PTY LTD; MCCARTHY, Thomas David; NAYLOR, Alan
Patent: WO2013/102242 A1, 2013 ;
反应条件
1: 94 percent / trichloroisocyanuric acid; 2,2,6,6-tetramethyl-1-piperidinoxyl / CH2Cl2 / 0.33 h / 0 °C
2: 56 percent / tetrabutylammonium fluoride / 24 h / 0 - 20 °C
3: 94 percent / NaBH4; LiCl / ethanol; tetrahydrofuran / 18 h / 20 °C
4: 89 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 18 h / 20 °C
5: NaH / tetrahydrofuran / 2 h / 0 - 20 °C
6: potassium tert-butoxide / tetrahydrofuran / 2 h / -40 °C
7: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
8: H2 / Raney-Ni / methanol
9: 94 percent / NaOCl; NaClO2; 2,2,6,6-tetramethyl-1-piperidinoxyl / acetonitrile; aq. phosphate buffer / 24 h / 45 °C / pH 6.7
View Scheme
参考文献
Del Valle, Juan R.; Goodman, Murray
Angewandte Chemie - International Edition, 2002 , vol. 41, # 9 p. 1600 - 1602
反应条件
1.1: lithium borohydride / tetrahydrofuran / 26 h / 0 - 20 °C
2.1: pyridine / dichloromethane / 18 h / 40 °C
3.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
4.1: triethylamine / dichloromethane / 0.5 h / 0 °C
5.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
5.2: 18 h
6.1: hydrogenchloride / methanol; 1,4-dioxane / 0.5 h / 20 °C
View Scheme
参考文献
Beinat, Corinne; Banister, Samuel D.; McErlean, Christopher S.P.; Kassiou, Michael
Tetrahedron Letters, 2013 , vol. 54, # 39 p. 5345 - 5347
反应条件
1: 81 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 / Ambient temperature
2: 89 percent / DAST / CH2Cl2 / -78 deg C to r.t.
3: 95 percent / LiOH / acetonitrile; H2O / Ambient temperature
4: TFA / CH2Cl2
View Scheme
参考文献
Demange, Luc; Menez, Andre; Dugave, Christophe
Tetrahedron Letters, 1998 , vol. 39, # 10 p. 1169 - 1172
